1-phenylhex-5-ene-1,3-diol | 948050-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-phenylhex-5-ene-1,3-diol
• 英文别名: 1-phenyl-5-hexen-1,3-diol；1-phenylhex-5-en-1,3-diol
• CAS: 948050-79-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XIBFDHGRGQMQBU-UHFFFAOYSA-N

物化性质

• 沸点：
  345.0±42.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenylhex-5-ene-1,3-diol 在 盐酸 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 41.0h， 生成 1-phenylhex-5-ene-1,3-diol
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans

  摘要：

  An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.

  DOI：

  10.1021/acs.joc.5b02371
• 作为产物：
  描述：

  1-phenyl-3-(phenylthio)-3<(2-propenyl)oxy>-1-propanol 在 lithium dihydronaphthylide radical 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到1-phenylhex-5-ene-1,3-diol
  参考文献：
  名称：

  Hoffmann, Rolf; Brueckner, Reinhard, Chemische Berichte, 1992, vol. 125, # 6, p. 1471 - 1484

  摘要：

  DOI：

文献信息

• Total synthesis of (+/−)-diospongin A via Prins reaction
  作者：Marie-Aude Hiebel、Béatrice Pelotier、Olivier Piva

  DOI：10.1016/j.tet.2007.05.089

  日期：2007.8

  A straightforward synthesis of (+/−)-diospongin A starting from benzaldehyde is described. A Prins cyclization reaction to control the relative configuration of the three stereogenic centers and a Mitsunobu inversion represent the key steps of the approach.

  描述了一种从苯甲醛开始的直接合成（+/-）-双甘皂苷A的方法。控制三个立体生成中心相对构型的Prins环化反应和Mitsunobu反转代表了该方法的关键步骤。
• Gold-catalyzed cycloisomerizations of ene-ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2008.10.108

  日期：2009.2

  The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates possessing a propargylic alcohol moiety. High diastereoselectivities are observed with 1,6-ene-ynamides having a stereocenter at the α or β position

  1，6-烯-酰胺的金催化的环异构化在温和的条件下进行，并从末端或三甲基甲硅烷基取代的酰胺中产生环丁酮，或从具有炔丙醇部分的底物上产生带有2,3-甲基吡咯烷亚基的羰基化合物。用在氮原子的α或β位置具有立体中心的1，6-烯-酰胺具有高的非对映选择性。
• Stereoselective synthesis of anti-1,3-diolsvia allylboration
  作者：George W Kabalka、C. Narayana、N.Kesavulu Reddy

  DOI：10.1016/0040-4039(96)00225-0

  日期：1996.3

  Allylboration of β-hydroxy aldehydes and ketones with allylboronic acid at room temperature produces the corresponding anti-1,3-diols as the major products.

  在室温下用烯丙基硼酸对β-羟基醛和酮进行烯丙基硼化反应，生成相应的抗-1,3-二醇作为主要产物。
• Strained Silacycles in Organic Synthesis:  The Tandem Aldol−Allylation Reaction
  作者：Xiaolun Wang、Qinglin Meng、Andrew J. Nation、James L. Leighton

  DOI：10.1021/ja027655f

  日期：2002.9.1

  Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol-allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon-carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.
• Diastereoselective Gold-Catalyzed Cycloisomerizations of Ene-Ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1002/anie.200602270

  日期：2006.10.13